For has long there have been sport or games of chance people have placed wages on them but what about organized betting? Did the Romans have something akin to bookies operating at arenas and if they did was it regulated?

During the Empire there seems to have been a very ambivalent approach to gambling generally.

Various law texts forbade it completely, except for at the Circus and races, and during Saturnalia. In practice gambling took place daily in most taverns, over a variety of table games, in the Imperial palace and in the barracks of parts of the Rome garrison; no doubt it was rife throughout the outposts of the empire. It was not officially sanctioned, so there was no central control - even at the chariot races in Rome betting was on a purely private basis, not officially organised.

I suspect that the various laws forbidding dice and other games were in response to widespread fraud and sharp practices, but they did nothing to curb the problem (Claudius himself was a devotee of dice games). So, in short, gambling was rife, risky and unregulated.